EP0217018B1 - Procédé de préparation d'esters d'acide 3-aminoacrylique - Google Patents
Procédé de préparation d'esters d'acide 3-aminoacrylique Download PDFInfo
- Publication number
- EP0217018B1 EP0217018B1 EP86109527A EP86109527A EP0217018B1 EP 0217018 B1 EP0217018 B1 EP 0217018B1 EP 86109527 A EP86109527 A EP 86109527A EP 86109527 A EP86109527 A EP 86109527A EP 0217018 B1 EP0217018 B1 EP 0217018B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formula
- weight
- alkali
- parts
- acid esters
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- YTLYLLTVENPWFT-UPHRSURJSA-N (Z)-3-aminoacrylic acid Chemical class N\C=C/C(O)=O YTLYLLTVENPWFT-UPHRSURJSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 30
- -1 amine salts Chemical class 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 150000001447 alkali salts Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001450 anions Chemical group 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- ZJKIBABOSPFBNO-UHFFFAOYSA-N 3-hydroxyprop-2-enoic acid Chemical class OC=CC(O)=O ZJKIBABOSPFBNO-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- JODDVGWNUWGSMG-UHFFFAOYSA-N ethyl 2-(dimethylamino)prop-2-enoate Chemical class CCOC(=O)C(=C)N(C)C JODDVGWNUWGSMG-UHFFFAOYSA-N 0.000 description 3
- NINSPLAPBBAHEW-UHFFFAOYSA-N ethyl 3-hydroxyprop-2-enoate Chemical compound CCOC(=O)C=CO NINSPLAPBBAHEW-UHFFFAOYSA-N 0.000 description 3
- BNIPQHDMPLVAIY-UHFFFAOYSA-N ethyl 3-hydroxyprop-2-enoate;sodium Chemical class [Na].CCOC(=O)C=CO BNIPQHDMPLVAIY-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000005265 dialkylamine group Chemical group 0.000 description 2
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- SQNWFKZOFAOCHM-IHWYPQMZSA-N (Z)-3-amino-2-methylacrylic acid Chemical compound N/C=C(/C)C(O)=O SQNWFKZOFAOCHM-IHWYPQMZSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical class CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- PSMXGKUBAXWYNH-UHFFFAOYSA-N 2-(ethylamino)prop-2-enoic acid Chemical compound CCNC(=C)C(O)=O PSMXGKUBAXWYNH-UHFFFAOYSA-N 0.000 description 1
- LMNMCUVHRMHOBH-UHFFFAOYSA-N 2-aminopent-2-enoic acid Chemical compound CCC=C(N)C(O)=O LMNMCUVHRMHOBH-UHFFFAOYSA-N 0.000 description 1
- FEWFXBUNENSNBQ-UHFFFAOYSA-N 2-hydroxyacrylic acid Chemical class OC(=C)C(O)=O FEWFXBUNENSNBQ-UHFFFAOYSA-N 0.000 description 1
- ZJKIBABOSPFBNO-OWOJBTEDSA-N 3-Hydroxypropenoate Chemical class O\C=C\C(O)=O ZJKIBABOSPFBNO-OWOJBTEDSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- 150000004331 4-hydroxyquinolines Chemical class 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 1
- ZNMIFKKFGNALHJ-UHFFFAOYSA-N ethyl 3-piperidin-1-ylprop-2-enoate Chemical compound CCOC(=O)C=CN1CCCCC1 ZNMIFKKFGNALHJ-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- UTMZHSWEBBBOKY-UHFFFAOYSA-N methyl 3-(dimethylamino)-2-phenylprop-2-enoate Chemical compound COC(=O)C(=CN(C)C)C1=CC=CC=C1 UTMZHSWEBBBOKY-UHFFFAOYSA-N 0.000 description 1
- MPLINSNWHXEXEM-UHFFFAOYSA-N methyl 3-hydroxy-2-phenylprop-2-enoate;sodium Chemical compound [Na].COC(=O)C(=CO)C1=CC=CC=C1 MPLINSNWHXEXEM-UHFFFAOYSA-N 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- LDPYIOQGUZVLTB-UHFFFAOYSA-M sodium;3-hydroxyprop-2-enoate Chemical compound [Na+].OC=CC([O-])=O LDPYIOQGUZVLTB-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- QMKYBPDZANOJGF-UHFFFAOYSA-N trimesic acid Natural products OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
Claims (3)
- Procédé de préparation d'esters d'acides 3-amino-acryliques de formule générale :
- Procédé selon la revendication 1 ,caractérisé en ce qu'on ajoute les sels alcalins des esters d'acides β-hydroxyacryliques de formule (II) dans les solvants cités à la revendication 1 ,notamment dans de l'acétate d'éthyle, sous forme de la suspension obtenue lors de la prépara tion de (II).
- Procédé selon l'une des revendications 1 ou 2 , caractérisé en ce qu'on utilise les sels d'amines de formule (III) en un excès de 0,05 à 1,5 mole .
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3531067 | 1985-08-30 | ||
DE19853531067 DE3531067A1 (de) | 1985-08-30 | 1985-08-30 | Verfahren zur herstellung von 3-aminoacrylsaeureestern |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0217018A1 EP0217018A1 (fr) | 1987-04-08 |
EP0217018B1 true EP0217018B1 (fr) | 1991-03-06 |
Family
ID=6279793
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP86109527A Expired - Lifetime EP0217018B1 (fr) | 1985-08-30 | 1986-07-11 | Procédé de préparation d'esters d'acide 3-aminoacrylique |
Country Status (4)
Country | Link |
---|---|
US (1) | US4772711A (fr) |
EP (1) | EP0217018B1 (fr) |
JP (1) | JPH07116116B2 (fr) |
DE (2) | DE3531067A1 (fr) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE59001401D1 (de) * | 1989-03-23 | 1993-06-17 | Bayer Ag | Verfahren zur herstellung von beta-amino-acrylsaeureestern. |
JPH0742258B2 (ja) * | 1989-04-14 | 1995-05-10 | 宇部興産株式会社 | 3―置換アミノアクリル酸エステル類の製造法 |
DE4031723A1 (de) * | 1990-10-06 | 1992-04-09 | Basf Ag | Verfahren zur herstellung von (alpha),(beta)-ungesaettigten carbonylverbindungen |
DE4207852A1 (de) * | 1992-03-12 | 1993-09-16 | Bayer Ag | Verfahren zur herstellung von (beta)-aminoacrylsaeureestern |
AU2295999A (en) * | 1998-06-29 | 2000-01-17 | Sharad Kumar Vyas | Process for preparation of substituted propenoic acid esters |
US8071681B2 (en) | 2004-08-13 | 2011-12-06 | Exxonmobil Chemical Patents Inc. | Polymeric compositions including their uses and methods of production |
CN101020647B (zh) * | 2007-02-14 | 2011-03-30 | 杭州师范学院 | 一种β-环丙胺基丙烯酸(酯)的合成方法 |
US7601864B1 (en) | 2008-05-08 | 2009-10-13 | Ufc Corporation | Method for synthesizing 4,4-dihalogen-2-(dialkylamino)methylene-3-oxy-alkylbutyrate and derivatives thereof |
CN103833565B (zh) * | 2013-12-11 | 2015-06-17 | 浙江先锋科技股份有限公司 | 一种3-n,n-二甲氨基丙烯酸乙酯的制备方法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2987491A (en) * | 1956-08-07 | 1961-06-06 | Pittsburgh Plate Glass Co | Alkyd resins modified by beta amino crotonic esters of higher organic hydroxides |
GB1576334A (en) * | 1977-05-26 | 1980-10-08 | Ici Ltd | N-alkyl and n,n-dialkyl derivatives thereof process for the manufacture of p-hydroxyphenylglycine and |
US4319024A (en) * | 1979-03-29 | 1982-03-09 | Dynamit Nobel Aktiengesellschaft | Method of preparing β-alkoxyacrlonitriles |
DE2938872A1 (de) * | 1979-09-26 | 1981-04-16 | Riedel-De Haen Ag, 3016 Seelze | Verfahren zur herstellung von 4-hydroxyphenylglycin |
DE3037086A1 (de) * | 1980-10-01 | 1982-05-06 | Dynamit Nobel Ag, 5210 Troisdorf | 3-(m-chloranilino-)acrylsaeureaethylester und ein verfahren zu dessen herstellung |
-
1985
- 1985-08-30 DE DE19853531067 patent/DE3531067A1/de active Granted
-
1986
- 1986-07-11 EP EP86109527A patent/EP0217018B1/fr not_active Expired - Lifetime
- 1986-07-11 DE DE8686109527T patent/DE3677866D1/de not_active Expired - Lifetime
- 1986-08-19 US US06/898,139 patent/US4772711A/en not_active Expired - Fee Related
- 1986-08-28 JP JP61200259A patent/JPH07116116B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US4772711A (en) | 1988-09-20 |
JPS6251651A (ja) | 1987-03-06 |
DE3531067A1 (de) | 1987-03-05 |
DE3531067C2 (fr) | 1989-08-17 |
EP0217018A1 (fr) | 1987-04-08 |
DE3677866D1 (de) | 1991-04-11 |
JPH07116116B2 (ja) | 1995-12-13 |
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